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Nature communications. 2025 May 17;16(1):4593. doi: 10.1038/s41467-025-59033-5 Q115.72025

Electrochemical synthesis of allenyl silanes and allenyl boronic esters

全烯基硅烷和全烯基硼酸酯的电化学合成 翻译改进

Tingting Feng  1, Tony Biremond  1, Philippe Jubault  1, Thomas Poisson  2

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作者单位

  • 1 INSA Rouen Normandie, Univ. Rouen Normandie, CNRS, Normandie Univ., Institut CARMeN UMR 6064, F-76000, Rouen, France.
  • 2 INSA Rouen Normandie, Univ. Rouen Normandie, CNRS, Normandie Univ., Institut CARMeN UMR 6064, F-76000, Rouen, France. thomas.poisson@insa-rouen.fr.
  • DOI: 10.1038/s41467-025-59033-5 PMID: 40382354

    摘要 中英对照阅读

    Allenyl silanes and boronates are pivotal building blocks in organic synthesis. Nevertheless, their synthesis requires the manipulation of transition metal or highly reactive species. Hence, the development of more sustainable protocol is highly sought after. Here we show the electrochemical synthesis of allenyl silanes and allenyl boronic esters. This catalyst-free method proceeds under mild reaction conditions. The protocol for the synthesis of allenyl silanes shows an excellent efficiency and a good functional group tolerance. The allenyl silanes are isolated in good yields (28 examples, 45-95% yields) without the use of a transition metal catalyst and under mild reaction conditions. A similar protocol is developed for the synthesis of allenyl boronates, which are obtained in low to moderate yields (13 examples, 5-55% yields). Finally, a mechanism based on an oxidative generation of the silyl and boryl radicals is suggested to access these classes of allenes.

    Keywords:electrochemical synthesis; allenyl silanes; allenyl boronic esters

    亚烯基硅烷和硼酸酯是有机合成中的关键构建模块。然而,它们的合成通常需要操作过渡金属或高度反应性的物种。因此,开发更可持续的方法备受期待。在这里,我们展示了通过电化学方法合成亚烯基硅烷和亚烯基硼酸酯的过程。此催化剂-free方法在温和的反应条件下进行,并且用于合成亚烯基硅烷的方法表现出优异的效率和良好的官能团耐受性。亚烯基硅烷以良好的收率(28个例子,45-95%)分离出来,无需使用过渡金属催化剂并且在温和的反应条件下获得。类似地开发了一种合成亚烯基硼酸酯的方法,产物以较低到中等的产率得到(13个例子,5-55%)。最后,基于通过氧化生成硅基和硼基自由基的机制来访问这些类型的亚烯烃被提出。

    © 2025. The Author(s).

    关键词:电化学合成; 烯丙基硅烷; 烯丙基硼酸酯

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    期刊名:Nature communications

    缩写:NAT COMMUN

    ISSN:N/A

    e-ISSN:2041-1723

    IF/分区:15.7/Q1

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    Electrochemical synthesis of allenyl silanes and allenyl boronic esters